


Start living your romance novel

by Moeta



Series: Moeta's fictober [3]
Category: Critical Role (Web Series)
Genre: Caleb Widogast Deserves Nice Things, F/M, Fictober, Fictober 2019, Highschool AU, Love Story, Widojest - Freeform, Wingman Beauregard
Language: English
Status: Completed
Published: 2019-10-03
Updated: 2019-10-03
Packaged: 2020-11-23 02:51:00
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,963
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20884913
Author URL: https://archiveofourown.org/users/Moeta/pseuds/Moeta
Summary: “Beau told me you were considering not going, and I’m just going full on dictator now, you’re going.”, Jester turned her innocent eyes into intimidating ones, a change that wasn’t all too powerful rather it just made her look even more cute.“I get no choice?”,“Nope, none at all”, Jester pulled a sly smirk,





	Start living your romance novel

**Author's Note:**

> Rated Teen beacuse of alcohol
> 
> Fictober 2019, Day 3: "Now? Now you listen to me?"
> 
> Hope you enjoy!

It’s a regular thursday just before lunch at Solstryce high. The winter season is waiting just around the corner presumably ready with a sudden violent storm to really kick off the cold times. Caleb Widogast sat in class. He was already more than done with whatever homework the teacher had given them, as he glanced around the class his eyes fell upon the usual. He would often spend the last few moments of class looking between the clock and his blue-haired co-student, Jester everyone called her, while she doodled away.

The bell began ringing to signal the end of class. Zeenoth of course objected to it dismissing them all, but his voice was all but nothing worth after the bell rung.

Almost everyone had left even before the bell stopped ringing. Jessie had been busy just finishing up her doodle of Zeenoth preaching about jurassic dicks, as far as Caleb could spy over her shoulder at least. 

Caleb was about to retreat from his spying position right behind Jester to get lunch, when he got a shove in the back by someone passing behind him knocking him into Jester just as she was getting out of her chair.

“Oh, ehm, err- sorry, didn’t mean to”, Caleb mumbled almost incomprehensibly, as he tried to turn around and leave only to fall spectacularly onto his face, as he tripped over nothing. “ _ Just, great _ ”, he thought.

All the while Jester tried to respond that it was fine but couldn’t help but laugh as he fell. “Are you okay o’Cayleb?”, she asked with a soft giggle.

Zeenoth could be found watching all this occur, not know what to do and silently leave the class.

“Ja, I’m all good, just tripped over my own two feet I guess”, they both looked down to see that his shoes had been tied together.

They both commented at the same time, “Of course” sighed Caleb, “heh, nice”, said Jester with a delightful smirk.

Caleb began retying his laces, as Jester waited for him with her bag on her shoulders. The classroom was silent with only the two of them left in it, Jester decided to break the silence, “man Zeenoth can be boring sometimes”.

  
“He sure can, but at least you got the essential, eh?”, Caleb nodded to the notebook that was sticking out of her bag slightly. “ _ Jurassic dicks _ , truly a masterpiece of cinematic works, wouldn’t you agree?”, Caleb joked smoothly all the while he was freaking out internally, he wasn’t supposed to be smooth.

“Yeah, I know right!”, Jester agreed, “now come-on let’s get to lunch this here lady needs some  _ donuts _ ”, her accented tickled Caleb just the right way, so that he couldn’t refuse.

As they sat down for lunch, one with donuts and others with the free fruit. Caleb looked out to see if he could spot his usual lunch-time eating partner but Beau was nowhere to be found in the eating hall. Caleb new he couldn’t do this anymore, he had already used up years worth of his cool and smoothness.

But Caleb couldn’t just leave that would be even more awkward so he relented to just sitting and nodding while Jester talked. During this time Caleb realised that he had been crushing on Jester for essentially all the time he had known of her. Everyone knew she had a thing for Fjord, the commander in chief of the school swim team, he had been brought up by the coach herself so that wasn’t surprising.

Jester could really speak a lot, even while her mouth was half-stuffed with a donut. she spoke of her art teacher, friend and amateur coach who went by the pseudonym of “the traveler”. This interesting woman didn’t make it easy to lose a crush on her.

The bell rung, “it was nice speaking to you Cayleb!” Jester’s muffled voice said as she quickly stuffed the last donut into her mouth and ran for gym class. Caleb on the other hand, did not sprint for gym class, if you asked him, then it shouldn’t be on the schedule but alas the world is what it is. That didn’t stop him from getting to it at the latest possible moment.

As Caleb slowly wandered down the hall a hand fell on his shoulder, Caleb looked back and saw the tall, tan, big sister figure that was Beauregard. “How did it feel when you fell for Jester?”, Beau shot him a smirk, “or however that one goes”, Beau stuck out her tongue but swiftly retracted it again.

“Of course it was you”, Caleb sighed, “where were you during lunch? I needed backup in the situation you put me in”

“Did you really? You did fine if you ask me”, Beau gave him a sly smile, “not that I’m the expert but I’m a firm believer that you really needed a push, one that I’m more than willing to give you”. Caleb felt the shoulder shove before Beau even touched him. “Seriously though, wasn’t today just slightly awesome?”, she offered.

“Slightly”, Caleb agreed reluctantly, “ but also very much terrifying”.

Just before the two split for each their own dressing rooms, Beauregard added, “remember there’s a party like thing friday”, and then she was gone behind the girls’ door.

Caleb stayed still as most he could during gym, his frail ginger self wasn’t built for sport and he was fine with that. Beside that excuse, doing little also gave him time to weigh his options concerning friday and more specifically Jester.

“ _ This isn’t a romance novel _ ”, he thought to himself, “ _ I should think as if it were _ ”. In his deep thought he didn’t notice someone sneaking up on him, “Watcha doin’ Cayleb?”, Jester’s voice nearly made him job out of his skin. “Either you’re have a pretty bizarre workout regime your practicing involving getting scared, or maybe you are doing something even more important that gym class?”.

“I don’t know how to explain it, but I might not be doing gym class no”, Caleb answered her.

“Oooh, the plot thickens. Might it be something concerning friday night?”, Jester stood on her tippy toes and gave Caleb some incredibly innocent eyes.

“ehm, that-, ye-yeah that would describe it I guess, how’d you know?”

“Beau told me you were considering not going, and I’m just going full on dictator now, you’re going.”, Jester turned her innocent eyes into intimidating ones, a change that wasn’t all too powerful rather it just made her look even more cute.

“I get no choice?”,

“Nope, none at all”, Jester pulled a sly smirk,

“Well that settles it then, I’m going”, 

at that Jester’s smirk turned into a genuine smile, “great! See you there then”.

The rest of gym went by in the blink of an eye, Caleb couldn’t really focus the rest of the day making it all fly by.

When he got home he was met by his little brave sister, Veth. Veth, being the best keeper of secrets as well the wisest person Caleb knew, got everything Jester and friday related told to her. Even in her young 9 years of age she knew exactly what he should do, “just do it or get drunk and then just do it. You can always blame it on the liquor“, it was a bit frightening to have your little sister tell you to get drunk to score your crush.

Friday came around, it was a holiday, perfect for a party. Caleb didn’t know how to dress so he used all day, texting Beau and nagging his little sister until just settling on a simple old plaid shirt with a t-shirt beneath it, Caleb even shaved his weird and shaggy mix of stubble and beard.

The party was at Molly’s house, Molly being the president of the student council and a master debater on the debate team. The party was supposed to start at 18 o’clock, so Caleb showed up 17 o’clock. Molly didn’t bother him with that, Caleb was just put to work, helping to put everything up. While doing that Molly too heard what was at stake for Caleb for the night. Caleb’s nerves were making him a tattle tail on himself, this gave him yet another worry for the night, that Jester would he about it and it would all blow up before he even got his small, drunk chance.

Party hour came and suddenly Molly’s house and garden were buzzing with buzzed people. The worst part, Jester was nowhere to be seen.

If Jester didn’t show up and the word spread, which it undoubtedly would at a party like this, then Caleb was already ruined, so he might as well get past that point of drunkenness that he had previously planned.

As Caleb began to consume vast amounts of alcohol there were two pairs of arms on him only a few moments later, Molly to his left and Beau to his right, “I just want to forget tonight”, Caleb answered the question before they asked it.

“Why do you want to forget tonight?”, the sweet unforgettable voice of Jester sounded behind him, making him swallow.

“Now? now you listen to me?” Caleb asked, the drunkenly chosen words turning his question into an accusation. Molly and Beau both squeezed his arms a bit before releasing him as he said that.

“I’m sorry Cayleb, I didn’t mean to snoop”, Caleb felt guilty at hearing her sound so sorry for something that was entirely his fault.

“It wasn’t- I-, I just gave up on something tonight and you just proved there actually was a hope that I then utterly destroyed”. Caleb sunk into himself a bit.

Jester thought for a minute, “I think you need a break from all of this”, she grabbed his hand and let him out to the front porch, out into the cold, fresh air.

“I’m sorry”, Caleb said out into the void

“I’m sorry too”, Jester responded

“You haven’t done anything wrong”,

“What were you hoping for that you then, perhaps utterly destroyed?”, Jester asked as she sat down on the cold hard concrete road.

“I think I was hoping I was living in a romance novel I guess”, Caleb said as he slumped down to join her.

“And how can you spoil that? Every novel is a romance novel and everyone is living their own novel”, Jester explained waving her hands around.

“Oh so saying I like you, will magically make them like me?”, while waving his arms around too.

“Yup, just like that. I mean people like being liked so there’s that, but it also helps when you’re cute Cayleb”,

“Aaah, well then I don’t really meet the magical requirements then”,

“Cayleb, a second ago you didn’t believe in magic now you believe you don’t meet its standards?”,

“Yup”,

“Now this might just be the alcohol talking, Caleb Widogast, but I like you too, dingus”,

“wha-what?”,

“Now? Now you listen to me?”, Jeste mocked with a giggle, “now come on, let us get in, get more drunk and how about you start living your romance novel?”.

As they both got up snow began to fall slowly, like the curtains after a play. Caleb quickly thought of the most romance novel thing he could do. He laid his hands softly onto Jester’s shoulder “Jester Lavorre, I really like you”,

“Caleb Widogast, I like you too, dingus”, she repeated sticking out her tongue.

They both leaned in for a kiss and Molly and Beau who had been spying from the inside of the house could both agree on what that kissing scene looked like, it even ended with a fade to black as the porch light went out for not sensing any movement for too long.

And it wasn’t just the alcohol that made Jester say that.

**Author's Note:**

> Heyo! Thanks for reading :~)
> 
> I'd if you could comment and give me any and all feedback, who knows I might end up keep doing this after fictober


End file.
